Conventional operating systems permit users to view multiple computing applications through windows. Each of these windows generally includes a frame or control for selecting which window is focused or to move, size, or otherwise manage placement of the window with respect to a workspace and other windows. These frames or controls, however, often only enable interaction with a currently active window and can result in unintended occlusion and overlap between the windows. Moreover, underlying applications associated with windows may be suspended in some cases and generally must be launched and running before content may be manipulated via the applications. Accordingly, interaction with multiple windows to handle content items may require a user to perform a series of tasks to activate, launch, position, and/or size each window as desired. As such, managing the layout of multiple windows in this fashion can be overly complicated, time-consuming, and frustrating to users.